AU2011249733B2 - Low temperature cure heat-curable powder coating composition comprising a crystalline polyester resin, an amorphous polyester resin, a crosslinking agent and a thermal radical initiator - Google Patents
Low temperature cure heat-curable powder coating composition comprising a crystalline polyester resin, an amorphous polyester resin, a crosslinking agent and a thermal radical initiator Download PDFInfo
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- AU2011249733B2 AU2011249733B2 AU2011249733A AU2011249733A AU2011249733B2 AU 2011249733 B2 AU2011249733 B2 AU 2011249733B2 AU 2011249733 A AU2011249733 A AU 2011249733A AU 2011249733 A AU2011249733 A AU 2011249733A AU 2011249733 B2 AU2011249733 B2 AU 2011249733B2
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- Prior art keywords
- polyester resin
- crystalline
- crosslinking agent
- composition
- acid
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- 239000000843 powder Substances 0.000 title claims abstract description 128
- 229920001225 polyester resin Polymers 0.000 title claims abstract description 113
- 239000004645 polyester resin Substances 0.000 title claims abstract description 113
- 239000003431 cross linking reagent Substances 0.000 title claims abstract description 95
- 239000008199 coating composition Substances 0.000 title claims abstract description 77
- 239000003999 initiator Substances 0.000 title claims abstract description 30
- 238000013035 low temperature curing Methods 0.000 title description 3
- 239000000203 mixture Substances 0.000 claims abstract description 180
- 239000002253 acid Substances 0.000 claims abstract description 107
- 238000000576 coating method Methods 0.000 claims abstract description 69
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 54
- 229920000728 polyester Polymers 0.000 claims description 54
- 239000000758 substrate Substances 0.000 claims description 53
- 239000011248 coating agent Substances 0.000 claims description 44
- 235000011087 fumaric acid Nutrition 0.000 claims description 40
- 150000003254 radicals Chemical class 0.000 claims description 38
- 150000002978 peroxides Chemical group 0.000 claims description 36
- -1 transition metal salts Chemical class 0.000 claims description 32
- 238000000034 method Methods 0.000 claims description 28
- 239000002245 particle Substances 0.000 claims description 19
- 238000002360 preparation method Methods 0.000 claims description 17
- 239000003112 inhibitor Substances 0.000 claims description 16
- 229910052723 transition metal Inorganic materials 0.000 claims description 16
- 238000010438 heat treatment Methods 0.000 claims description 15
- 150000002976 peresters Chemical class 0.000 claims description 13
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical group C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 claims description 11
- 150000003624 transition metals Chemical class 0.000 claims description 11
- 150000003623 transition metal compounds Chemical class 0.000 claims description 10
- 229920001567 vinyl ester resin Polymers 0.000 claims description 8
- 229960000834 vinyl ether Drugs 0.000 claims description 8
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 7
- 238000001816 cooling Methods 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- RSJKGSCJYJTIGS-UHFFFAOYSA-N undecane Chemical compound CCCCCCCCCCC RSJKGSCJYJTIGS-UHFFFAOYSA-N 0.000 claims description 6
- 150000005206 1,2-dihydroxybenzenes Chemical class 0.000 claims description 5
- 150000005208 1,4-dihydroxybenzenes Chemical class 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 229910052802 copper Inorganic materials 0.000 claims description 5
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 150000004054 benzoquinones Chemical class 0.000 claims description 4
- 230000000052 comparative effect Effects 0.000 claims description 4
- 229910052742 iron Inorganic materials 0.000 claims description 4
- 229910052748 manganese Inorganic materials 0.000 claims description 4
- 238000002156 mixing Methods 0.000 claims description 4
- 150000002989 phenols Chemical class 0.000 claims description 4
- 150000002990 phenothiazines Chemical class 0.000 claims description 3
- 238000000227 grinding Methods 0.000 claims description 2
- 238000013007 heat curing Methods 0.000 abstract description 8
- 229920005989 resin Polymers 0.000 description 66
- 239000011347 resin Substances 0.000 description 66
- 239000011572 manganese Substances 0.000 description 45
- 238000001723 curing Methods 0.000 description 24
- 229920000642 polymer Polymers 0.000 description 24
- 239000000178 monomer Substances 0.000 description 20
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 20
- 150000001875 compounds Chemical class 0.000 description 18
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
- 239000001530 fumaric acid Substances 0.000 description 13
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 13
- 238000002844 melting Methods 0.000 description 13
- 230000008018 melting Effects 0.000 description 13
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 11
- 229920006337 unsaturated polyester resin Polymers 0.000 description 11
- 239000002023 wood Substances 0.000 description 11
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 10
- 229920006127 amorphous resin Polymers 0.000 description 10
- 239000003054 catalyst Substances 0.000 description 10
- 229920006038 crystalline resin Polymers 0.000 description 10
- 230000000977 initiatory effect Effects 0.000 description 10
- 229910052751 metal Inorganic materials 0.000 description 10
- 239000002184 metal Substances 0.000 description 10
- 239000003795 chemical substances by application Substances 0.000 description 9
- 229920003023 plastic Polymers 0.000 description 9
- 239000004033 plastic Substances 0.000 description 9
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 8
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 8
- 150000007513 acids Chemical class 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 8
- 230000032050 esterification Effects 0.000 description 8
- 238000005886 esterification reaction Methods 0.000 description 8
- 238000005259 measurement Methods 0.000 description 8
- 229910052757 nitrogen Inorganic materials 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- 229910052782 aluminium Inorganic materials 0.000 description 7
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 7
- 229910052799 carbon Inorganic materials 0.000 description 7
- 238000007373 indentation Methods 0.000 description 7
- LVHBHZANLOWSRM-UHFFFAOYSA-N itaconic acid Chemical compound OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 7
- 239000007788 liquid Substances 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- 238000003786 synthesis reaction Methods 0.000 description 7
- 239000012974 tin catalyst Substances 0.000 description 7
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 6
- 150000001298 alcohols Chemical class 0.000 description 6
- 229920006125 amorphous polymer Polymers 0.000 description 6
- 150000008064 anhydrides Chemical class 0.000 description 6
- HNEGQIOMVPPMNR-IHWYPQMZSA-N citraconic acid Chemical compound OC(=O)C(/C)=C\C(O)=O HNEGQIOMVPPMNR-IHWYPQMZSA-N 0.000 description 6
- 238000004821 distillation Methods 0.000 description 6
- 239000011888 foil Substances 0.000 description 6
- 230000009477 glass transition Effects 0.000 description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 6
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 6
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 6
- 239000011976 maleic acid Substances 0.000 description 6
- 229940117969 neopentyl glycol Drugs 0.000 description 6
- 125000000962 organic group Chemical group 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 150000005846 sugar alcohols Polymers 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- 238000005160 1H NMR spectroscopy Methods 0.000 description 5
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
- 239000004971 Cross linker Substances 0.000 description 5
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 5
- 150000001735 carboxylic acids Chemical class 0.000 description 5
- 239000010949 copper Substances 0.000 description 5
- 238000002425 crystallisation Methods 0.000 description 5
- 230000008025 crystallization Effects 0.000 description 5
- 239000004417 polycarbonate Substances 0.000 description 5
- 239000007921 spray Substances 0.000 description 5
- 125000001424 substituent group Chemical group 0.000 description 5
- 229920001187 thermosetting polymer Polymers 0.000 description 5
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 4
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 4
- 125000004429 atom Chemical group 0.000 description 4
- 238000004132 cross linking Methods 0.000 description 4
- 230000001419 dependent effect Effects 0.000 description 4
- 238000000113 differential scanning calorimetry Methods 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 150000002894 organic compounds Chemical class 0.000 description 4
- 230000005855 radiation Effects 0.000 description 4
- GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-UHFFFAOYSA-N 0.000 description 4
- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 description 4
- HMBNQNDUEFFFNZ-UHFFFAOYSA-N 4-ethenoxybutan-1-ol Chemical compound OCCCCOC=C HMBNQNDUEFFFNZ-UHFFFAOYSA-N 0.000 description 3
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 239000004698 Polyethylene Substances 0.000 description 3
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 3
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 3
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 3
- 150000001991 dicarboxylic acids Chemical class 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 150000002009 diols Chemical class 0.000 description 3
- 239000004744 fabric Substances 0.000 description 3
- 125000005842 heteroatom Chemical group 0.000 description 3
- 150000002432 hydroperoxides Chemical class 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 3
- HNEGQIOMVPPMNR-NSCUHMNNSA-N mesaconic acid Chemical compound OC(=O)C(/C)=C/C(O)=O HNEGQIOMVPPMNR-NSCUHMNNSA-N 0.000 description 3
- 239000000049 pigment Substances 0.000 description 3
- 229920000515 polycarbonate Polymers 0.000 description 3
- 238000006068 polycondensation reaction Methods 0.000 description 3
- 239000004814 polyurethane Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 229960004063 propylene glycol Drugs 0.000 description 3
- 235000013772 propylene glycol Nutrition 0.000 description 3
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 3
- 229920006126 semicrystalline polymer Polymers 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 2
- PXGZQGDTEZPERC-UHFFFAOYSA-N 1,4-cyclohexanedicarboxylic acid Chemical compound OC(=O)C1CCC(C(O)=O)CC1 PXGZQGDTEZPERC-UHFFFAOYSA-N 0.000 description 2
- PTBDIHRZYDMNKB-UHFFFAOYSA-N 2,2-Bis(hydroxymethyl)propionic acid Chemical compound OCC(C)(CO)C(O)=O PTBDIHRZYDMNKB-UHFFFAOYSA-N 0.000 description 2
- ICKWICRCANNIBI-UHFFFAOYSA-N 2,4-di-tert-butylphenol Chemical compound CC(C)(C)C1=CC=C(O)C(C(C)(C)C)=C1 ICKWICRCANNIBI-UHFFFAOYSA-N 0.000 description 2
- SGWZVZZVXOJRAQ-UHFFFAOYSA-N 2,6-Dimethyl-1,4-benzenediol Chemical compound CC1=CC(O)=CC(C)=C1O SGWZVZZVXOJRAQ-UHFFFAOYSA-N 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- HRDCVMSNCBAMAM-UHFFFAOYSA-N 3-prop-2-ynoxyprop-1-yne Chemical compound C#CCOCC#C HRDCVMSNCBAMAM-UHFFFAOYSA-N 0.000 description 2
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- 229920000742 Cotton Polymers 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
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- YIVJZNGAASQVEM-UHFFFAOYSA-N Lauroyl peroxide Chemical compound CCCCCCCCCCCC(=O)OOC(=O)CCCCCCCCCCC YIVJZNGAASQVEM-UHFFFAOYSA-N 0.000 description 2
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- 150000007524 organic acids Chemical class 0.000 description 1
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- 239000004482 other powder Substances 0.000 description 1
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- 239000003973 paint Substances 0.000 description 1
- 239000000123 paper Substances 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 229950000688 phenothiazine Drugs 0.000 description 1
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 1
- XRBCRPZXSCBRTK-UHFFFAOYSA-N phosphonous acid Chemical class OPO XRBCRPZXSCBRTK-UHFFFAOYSA-N 0.000 description 1
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- OPQYOFWUFGEMRZ-UHFFFAOYSA-N tert-butyl 2,2-dimethylpropaneperoxoate Chemical compound CC(C)(C)OOC(=O)C(C)(C)C OPQYOFWUFGEMRZ-UHFFFAOYSA-N 0.000 description 1
- KXYJPVZMZBJJBZ-UHFFFAOYSA-N tert-butyl 2-ethylbutaneperoxoate Chemical compound CCC(CC)C(=O)OOC(C)(C)C KXYJPVZMZBJJBZ-UHFFFAOYSA-N 0.000 description 1
- UWNNZXDNLPNGQJ-UHFFFAOYSA-N tert-butyl 2-ethylhexanoate Chemical compound CCCCC(CC)C(=O)OC(C)(C)C UWNNZXDNLPNGQJ-UHFFFAOYSA-N 0.000 description 1
- VNJISVYSDHJQFR-UHFFFAOYSA-N tert-butyl 4,4-dimethylpentaneperoxoate Chemical compound CC(C)(C)CCC(=O)OOC(C)(C)C VNJISVYSDHJQFR-UHFFFAOYSA-N 0.000 description 1
- SWAXTRYEYUTSAP-UHFFFAOYSA-N tert-butyl ethaneperoxoate Chemical compound CC(=O)OOC(C)(C)C SWAXTRYEYUTSAP-UHFFFAOYSA-N 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- UGNWTBMOAKPKBL-UHFFFAOYSA-N tetrachloro-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(Cl)=C(Cl)C1=O UGNWTBMOAKPKBL-UHFFFAOYSA-N 0.000 description 1
- UFDHBDMSHIXOKF-UHFFFAOYSA-N tetrahydrophthalic acid Natural products OC(=O)C1=C(C(O)=O)CCCC1 UFDHBDMSHIXOKF-UHFFFAOYSA-N 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 230000008646 thermal stress Effects 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 239000004634 thermosetting polymer Substances 0.000 description 1
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- 150000003568 thioethers Chemical class 0.000 description 1
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- 229910052719 titanium Inorganic materials 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- LRXTYHSAJDENHV-UHFFFAOYSA-H zinc phosphate Chemical compound [Zn+2].[Zn+2].[Zn+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O LRXTYHSAJDENHV-UHFFFAOYSA-H 0.000 description 1
- 229910000165 zinc phosphate Inorganic materials 0.000 description 1
- DRDVZXDWVBGGMH-UHFFFAOYSA-N zinc;sulfide Chemical compound [S-2].[Zn+2] DRDVZXDWVBGGMH-UHFFFAOYSA-N 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D167/00—Coating compositions based on polyesters obtained by reactions forming a carboxylic ester link in the main chain; Coating compositions based on derivatives of such polymers
- C09D167/02—Polyesters derived from dicarboxylic acids and dihydroxy compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L67/00—Compositions of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Compositions of derivatives of such polymers
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D167/00—Coating compositions based on polyesters obtained by reactions forming a carboxylic ester link in the main chain; Coating compositions based on derivatives of such polymers
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D167/00—Coating compositions based on polyesters obtained by reactions forming a carboxylic ester link in the main chain; Coating compositions based on derivatives of such polymers
- C09D167/06—Unsaturated polyesters having carbon-to-carbon unsaturation
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/01—Use of inorganic substances as compounding ingredients characterized by their specific function
- C08K3/011—Crosslinking or vulcanising agents, e.g. accelerators
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
- C08K5/0025—Crosslinking or vulcanising agents; including accelerators
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/06—Ethers; Acetals; Ketals; Ortho-esters
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/10—Esters; Ether-esters
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/10—Esters; Ether-esters
- C08K5/101—Esters; Ether-esters of monocarboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/14—Peroxides
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L67/00—Compositions of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Compositions of derivatives of such polymers
- C08L67/06—Unsaturated polyesters
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Paints Or Removers (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Macromonomer-Based Addition Polymer (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP10162159 | 2010-05-06 | ||
| EP10162176.1 | 2010-05-06 | ||
| EP10162159.7 | 2010-05-06 | ||
| EP10162176 | 2010-05-06 | ||
| PCT/EP2011/057294 WO2011138432A1 (en) | 2010-05-06 | 2011-05-06 | Low temperature cure heat-curable powder coating composition comprising a crystalline polyester resin, an amorphous polyester resin, a crosslinking agent and a thermal radical initiator |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU2011249733A1 AU2011249733A1 (en) | 2012-11-22 |
| AU2011249733B2 true AU2011249733B2 (en) | 2013-12-05 |
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| AU2011249733A Active AU2011249733B2 (en) | 2010-05-06 | 2011-05-06 | Low temperature cure heat-curable powder coating composition comprising a crystalline polyester resin, an amorphous polyester resin, a crosslinking agent and a thermal radical initiator |
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| Country | Link |
|---|---|
| US (1) | US9296917B2 (xx) |
| EP (1) | EP2566923B1 (xx) |
| CN (2) | CN104830214A (xx) |
| AU (1) | AU2011249733B2 (xx) |
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| DK (1) | DK2566923T3 (xx) |
| ES (1) | ES2620237T3 (xx) |
| HK (2) | HK1180707A1 (xx) |
| NZ (1) | NZ603172A (xx) |
| PL (1) | PL2566923T3 (xx) |
| SI (1) | SI2566923T1 (xx) |
| WO (1) | WO2011138432A1 (xx) |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| EP2596960B1 (en) | 2011-11-25 | 2016-04-20 | Océ-Technologies B.V. | Reusable print medium and method of manufacturing thereof |
| EA030358B9 (ru) * | 2013-04-26 | 2018-09-28 | ДСМ АйПи АССЕТС Б.В. | Винилфункционализованные уретановые смолы для композиций порошковых покрытий |
| AU2015246201B2 (en) | 2014-04-16 | 2018-04-19 | Covestro (Netherlands) B.V. | 2K thermosetting powder coating compositions |
| US9951171B2 (en) | 2014-08-20 | 2018-04-24 | Resinate Materials Group, Inc. | Polyester polyols from recycled polymers and waste streams |
| WO2016028841A1 (en) | 2014-08-20 | 2016-02-25 | Resinate Materials Group, Inc. | Digestion of keratin |
| US9850400B2 (en) | 2014-08-20 | 2017-12-26 | Resinate Materials Group, Inc. | Digestion of keratin |
| US9890243B2 (en) | 2014-10-29 | 2018-02-13 | Resinate Materials Group, Inc. | Polymeric plasticizer compositions |
| US9580546B2 (en) | 2014-10-29 | 2017-02-28 | Resinate Materials Group, Inc. | Polymeric plasticizer compositions |
| EP3034551A1 (en) | 2014-12-17 | 2016-06-22 | Akzo Nobel Chemicals International B.V. | Powder mixture comprising organic peroxide |
| WO2016126756A1 (en) | 2015-02-03 | 2016-08-11 | The Board Of Trustees Of The University Of Illinois | Cyclic dynamic polyureas for polymeric urea processing |
| WO2017058504A1 (en) | 2015-10-02 | 2017-04-06 | Resinate Materials Group, Inc. | High performance coatings |
| EP3239226B1 (en) | 2016-04-29 | 2019-04-10 | Jotun A/S | Particulate coating |
| CN109153774B (zh) * | 2016-05-27 | 2020-12-25 | 帝斯曼知识产权资产管理有限公司 | 聚合物、方法、组合物和用途 |
| EP3272779A1 (de) | 2016-07-21 | 2018-01-24 | TIGER Coatings GmbH & Co. KG | Pulverlackformulierung |
| BR112019004806A2 (pt) | 2016-09-12 | 2019-06-04 | Resinate Mat Group Inc | alcoxilado de polifenol contendo mesclas e revestimentos |
| US10913859B2 (en) | 2016-09-28 | 2021-02-09 | Dsm Ip Assets B.V. | Thermosetting powder coating compositions comprising peroxydicarbonates |
| EP3376296A1 (en) * | 2017-03-13 | 2018-09-19 | TIGER Coatings GmbH & Co. KG | Non-impact printing device |
| EP3635065A1 (en) | 2017-05-15 | 2020-04-15 | Jotun A/S | Composition |
| EP3514206A1 (en) | 2018-01-19 | 2019-07-24 | TIGER Coatings GmbH & Co. KG | Thermoplastic |
| US11008474B2 (en) | 2018-12-19 | 2021-05-18 | Pison Stream Solutions Inc. | Multi-purpose flexibility additive for chemical coating compositions |
| US10947395B2 (en) | 2018-12-19 | 2021-03-16 | Pison Stream Solutions Inc. | Multi-functional flow modifier for chemical coating compositions |
| US11118071B2 (en) | 2018-12-19 | 2021-09-14 | Pison Stream Solutions Inc. | Multi-functional additive for mar and scratch resistance in chemical coating compositions |
| CN111370621B (zh) * | 2020-03-13 | 2022-02-08 | 江苏厚生新能源科技有限公司 | 3d打印多孔膜及制备方法、交联剂、锂电池、打印系统 |
| CN111484714A (zh) * | 2020-05-13 | 2020-08-04 | 华东理工大学 | 一种不饱和团状模塑料的低温成型方法 |
| CN113480922A (zh) * | 2021-07-08 | 2021-10-08 | 福建华峰新材料有限公司 | 一种低温粉末涂料及其在袜套上的应用 |
| CN115678327A (zh) * | 2022-11-17 | 2023-02-03 | 江西龙正科技发展有限公司 | 一种新型木家具用的粉末涂料 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5527324A (en) | 1978-08-17 | 1980-02-27 | Asahi Chem Ind Co Ltd | Composition for powder coating |
| GB8924984D0 (en) | 1989-11-06 | 1989-12-28 | Shell Int Research | Interpolymer latices from esters of(meth)acrylic acid and vinyl esters of branched chain carboxylic acids |
| US5304332A (en) | 1992-03-24 | 1994-04-19 | Morton International, Inc. | In-mold coatings with improved performance |
| BE1007373A3 (nl) | 1993-07-30 | 1995-05-30 | Dsm Nv | Stralingsuithardbare bindmiddelsamenstelling voor poederverfformuleringen. |
| NL1002153C2 (nl) | 1996-01-23 | 1997-08-04 | Dsm Nv | Stralingsuithardbare poederverfbindmiddelsamenstelling. |
| CA2250901C (en) | 1996-04-03 | 2005-12-27 | Herberts Gesellschaft Mit Beschrankter Haftung | Modified polyester resin/organic peroxide systems for powder coatings which are applicable to temperature sensitive and metallic substrates |
| US5714206A (en) | 1996-05-06 | 1998-02-03 | Morton International, Inc. | Two component powder coating system and method for coating wood therewith |
| US5922473A (en) * | 1996-12-26 | 1999-07-13 | Morton International, Inc. | Dual thermal and ultraviolet curable powder coatings |
| NL1007052C2 (nl) | 1997-09-17 | 1999-03-18 | Dsm Nv | Bindmiddelsamenstelling voor poederverfformuleringen. |
| US6017593A (en) * | 1998-03-31 | 2000-01-25 | Morton International, Inc. | Method for producing low gloss appearance with UV curable powder coatings |
| US6048949A (en) | 1998-05-11 | 2000-04-11 | Morton International, Inc. | Unsaturated polyester powder coatings with improved surface cure |
| US6194525B1 (en) | 1998-05-11 | 2001-02-27 | Ferro Corporation | Powder coating composition comprising unsaturated polyesters and uses thereof |
| US6235228B1 (en) | 1999-04-08 | 2001-05-22 | Morton International, Inc. | Method for on-mold coating molded articles with a coating powder as a liquid gel coat replacement |
| EP1125996A1 (en) * | 2000-02-09 | 2001-08-22 | Ucb, S.A. | Radiation curable powder compositions |
| US6472491B1 (en) | 2000-10-05 | 2002-10-29 | Eastman Chemical Company | Process for preparing ethylene interpolymers and ethylene interpolymers |
| US6608156B1 (en) | 2000-10-05 | 2003-08-19 | Eastman Chemical Company | Process for preparing interpolymers of ethylene and 2,3-dihydrofuran, or a heteroatom substituted olefin monomer and ethylene interpolymers |
| EP1148102A3 (en) | 2000-12-21 | 2002-06-05 | Dsm N.V. | Coating composition and coated substrate with good heat stability and colour |
| JPWO2002100956A1 (ja) | 2001-06-08 | 2004-09-24 | ダイキン工業株式会社 | 熱硬化型粉体塗料組成物 |
| MXPA03011239A (es) * | 2001-06-08 | 2004-02-26 | Du Pont | Revestimientos en polvo de radicales libres de bajo brillo. |
| EP1477534A3 (en) | 2003-05-16 | 2005-01-19 | Rohm And Haas Company | Multiple-part fast cure powder coatings |
| GB2423770A (en) | 2005-02-01 | 2006-09-06 | Ucn Know How Ltd | Crystalline or semi-crystalline polyurethane |
| DE102005049916A1 (de) | 2005-10-17 | 2007-04-19 | Degussa Gmbh | Lagerstabile, reaktive Pulverlackzusammensetzungen mit kristallinen Bestandteilen |
| MX2008014205A (es) | 2006-05-19 | 2008-11-14 | Basf Coatings Ag | Materiales de revestimiento en polvo con policarbonatos de alta funcionalidad, altamente ramificados o hiper-ramificados. |
| PL2342290T3 (pl) | 2008-11-07 | 2014-12-31 | Dsm Ip Assets Bv | Dwuskładnikowa kompozycja termoutwardzalnej farby proszkowej |
| PL2342288T3 (pl) * | 2008-11-07 | 2016-08-31 | Dsm Ip Assets Bv | Jednoskładnikowa, utwardzana termicznie proszkowa kompozycja powlekająca |
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2011
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- 2011-05-06 ES ES11717287.4T patent/ES2620237T3/es active Active
- 2011-05-06 CN CN201510249525.3A patent/CN104830214A/zh active Pending
- 2011-05-06 SI SI201131134A patent/SI2566923T1/sl unknown
- 2011-05-06 US US13/696,449 patent/US9296917B2/en active Active
- 2011-05-06 BR BR112012028431A patent/BR112012028431A2/pt not_active IP Right Cessation
- 2011-05-06 PL PL11717287T patent/PL2566923T3/pl unknown
- 2011-05-06 CN CN201180022834.7A patent/CN102884132B/zh active Active
- 2011-05-06 AU AU2011249733A patent/AU2011249733B2/en active Active
- 2011-05-06 EP EP11717287.4A patent/EP2566923B1/en active Active
- 2011-05-06 NZ NZ603172A patent/NZ603172A/xx unknown
- 2011-05-06 DK DK11717287.4T patent/DK2566923T3/en active
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2013
- 2013-07-03 HK HK13107801.9A patent/HK1180707A1/xx unknown
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2016
- 2016-02-05 HK HK16101441.5A patent/HK1213588A1/zh unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ES2620237T3 (es) | 2017-06-28 |
| US9296917B2 (en) | 2016-03-29 |
| EP2566923A1 (en) | 2013-03-13 |
| CN104830214A (zh) | 2015-08-12 |
| CN102884132B (zh) | 2015-06-17 |
| NZ603172A (en) | 2013-08-30 |
| HK1213588A1 (zh) | 2016-07-08 |
| CN102884132A (zh) | 2013-01-16 |
| WO2011138432A1 (en) | 2011-11-10 |
| AU2011249733A1 (en) | 2012-11-22 |
| DK2566923T3 (en) | 2017-03-27 |
| PL2566923T3 (pl) | 2017-07-31 |
| HK1180707A1 (en) | 2013-10-25 |
| US20130203938A1 (en) | 2013-08-08 |
| SI2566923T1 (sl) | 2017-04-26 |
| EP2566923B1 (en) | 2017-01-04 |
| BR112012028431A2 (pt) | 2019-09-24 |
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